WO2022124540A1 - Organic compound and organic light-emitting device comprising same - Google Patents

Abstract

The present invention relates to an organic compound and an organic light-emitting device comprising same, the organic compound being employed in an organic layer, such as an electron-transporting layer, in an organic light-emitting device and in a luminous efficiency-improving layer (a capping layer) provided in an organic light-emitting device to achieve light-emitting characteristics such as superior luminous efficiency and low-voltage driving of a device. The present invention can realize improved device characteristics such as superior luminous efficiency and low-voltage driving and thus can be industrially usefully employed in various lighting and display devices.

Description

Organic compound and organic light emitting device comprising same

The present invention relates to an organic compound, and more particularly, to an organic compound used as a material for an organic layer in an organic light emitting device, and a light efficiency improving layer (Capping layer) provided in the organic light emitting device, and a low voltage of the device by employing the same It relates to an organic light-emitting device having significantly improved light-emitting characteristics such as driving and excellent light-emitting efficiency.

The organic light emitting device can be formed on a transparent substrate as well as being able to drive at a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescent (EL) display, and consume relatively little power. , has the advantage of excellent color, and can represent three colors of green, blue, and red.

However, in order for such an organic light emitting device to exhibit the above characteristics, the material constituting the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material, is supported by stable and efficient materials. However, the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed.

Therefore, in order to realize a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, additional improvements are required in terms of efficiency and lifespan characteristics. It is desperately needed.

In addition, in recent years, not only research on improving the characteristics of an organic light emitting device by changing the performance of each organic layer material, but also improving color purity and increasing luminous efficiency by an optical thickness optimized between an anode and a cathode has been developed. It has been focused on one of the important factors for improving the performance, and as an example of this method, an increase in luminous efficiency and excellent color purity are achieved by using a capping layer on an electrode.

Therefore, the present invention is a novel organic compound capable of implementing excellent light emitting characteristics such as low voltage driving and improved light emitting efficiency of the device by being employed in an organic layer in an organic light emitting device or a light efficiency improving layer (Capping layer) provided in the organic light emitting device, and An object of the present invention is to provide an organic light emitting device including

The present invention provides an organic compound represented by the following [Formula I] in order to solve the above problems.

[Formula Ⅰ]

The characteristic structure of the [Formula I] and the compound implemented thereby, Ar, L, R ₁ to R ₂ will be described later.

When the organic compound according to the present invention is employed as an organic layer in an organic light emitting device or as a material for a light efficiency improvement layer provided in an organic light emitting device, it is possible to realize light emitting characteristics such as low voltage driving and excellent light emitting efficiency of the device, which is useful for various display devices. can be used

Hereinafter, the present invention will be described in more detail.

The present invention relates to an organic compound represented by the following [Formula I], which can achieve light emitting characteristics such as low voltage driving and excellent luminous efficiency of the organic light emitting device,

In the framework structure structurally represented by the following [Formula I], (1) an aryl derivative having at least one cyano group (CN) is necessarily introduced at the carbazole-N group, and (2) positions 1-4 of the carbazole (R ₂ ) and benzoxazole and/or benzothiazole derivatives are introduced at positions 5-8 of carbazole (R ₁ ). Efficiency characteristics can be improved.

[Formula Ⅰ]

In the [Formula I],

Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in which at least one cyano group (CN) is substituted, m is an integer of 1 or 2, and when m is 2, a plurality of Ars are the same as or different from each other do.

L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, n is an integer of 0 to 2, and when n is 2, a plurality of L's are the same or different from each other.

The compound according to the present invention is characterized in that an aryl structure (-(L) _n -(Ar) _m ) having at least one cyano group (CN) is necessarily introduced at the -N group of the carbazole in the [Formula I] skeleton do.

R ₁ to R ₂ are each independently represented by the following [Structural Formula 1].

[Structural Formula 1]

In the [Structural Formula 1],

X is O or S, Z is CR, and a plurality of R are the same or different from each other.

R and R ₃ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C 3 to 20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 halogenated alkyl group, substituted or unsubstituted C1-C20 halogenated alkoxy group, substituted or It is selected from an unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group.

Any one of the plurality of R and R ₃ is a moiety in which [Formula 1] is connected in [Formula I] at the positions of R ₁ and R ₂ , respectively.

In addition, the plurality of R and R ₃ may be bonded to each other or connected to an adjacent substituent to form an aromatic monocyclic or polycyclic ring, and thus [Formula 1] is represented by the following [Formula 2] to [Formula 6] It may be any one selected from the structural formulas shown.

[Structural formula 2] [Structural formula 3] [Structural formula 4]

[Structural formula 5] [Structural formula 6]

In the [Structural Formula 2] to [Structural Formula 6],

X is O or S, Z is CR, and a plurality of R are the same or different from each other.

R and R ₃ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C 3 to 20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 halogenated alkyl group, substituted or unsubstituted C1-C20 halogenated alkoxy group, substituted or It is selected from an unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group.

Any one of the plurality of R and R ₃ is a moiety in which [Formula 1] is connected in [Formula I] at the positions of R ₁ and R ₂ , respectively.

Meanwhile, in the definitions of Ar, L, R and R ₃ , 'substituted or unsubstituted' means deuterium, deuterium, halogen group, cyano group, nitro group, hydroxyl group, silyl group, alkyl group, halogenated alkyl group, heavy water One or two or more selected from the group consisting of a digested alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, an alkylamine group, an arylamine group, and a silyl group It means that it is substituted with a substituent, is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.

For specific examples, the substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, etc. are substituted with other substituents do.

In addition, the substituted heteroaryl group refers to a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and a condensed heterocyclic group thereof, such as a benzquinoline group. , a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with other substituents.

In the present invention, examples of the substituents will be described in detail below, but the present invention is not limited thereto.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present invention, the alkoxy group may be straight-chain or branched. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20 in a range that does not cause steric hindrance. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

In the present invention, a deuterated alkyl group or alkoxy group, halogenated alkyl group or alkoxy group means an alkyl group or alkoxy group in which the alkyl group or alkoxy group is substituted with deuterium or a halogen group.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, and a tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited only to these examples.

In the present invention, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, for example,

,

,

etc.

In the present invention, the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected through one atom. , for example

,

etc.

In addition, the carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O, for example,

,

,

,

etc.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N, or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and for a specific example thereof in the present invention, a thiophene group , furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyra Zinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadia and a zolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazine group, a phenothiazine group, and the like, but are not limited thereto.

In the present invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc., and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxy phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but is not limited thereto.

In the present invention, the amine group may be -NH ₂ , an alkylamine group, an arylamine group, etc., the arylamine group means an amine substituted with an aryl, the alkylamine group means an amine substituted with an alkyl, and an arylamine group Examples of these include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group, and the aryl group in the arylamine group is the same as the definition of the aryl group, , The alkyl group of the alkylamine group is also the same as the definition of the alkyl group.

Specific examples of the halogen group as a substituent used in the present invention include fluorine (F), chlorine (Cl), bromine (Br), and the like.

In the present invention, the cycloalkyl group refers to, and includes, monocyclic, polycyclic and spiro alkyl radicals, and preferably contains 3 to 20 ring carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirodecyl, adamantyl, and the like, wherein the cycloalkyl group may be optionally substituted.

In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, wherein one or more heteroatoms are O, S, N, P, B, Si, and Se , Preferably it is selected from O, N or S, and specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.

The organic compound according to the present invention represented by the [Formula I] can be used as various organic layers including the electron transport layer in the organic light emitting device due to its structural specificity, and can also be used as a material for the light efficiency improvement layer provided in the organic light emitting device can

Preferred examples of the organic compound represented by [Formula I] according to the present invention include the following compounds, but are not limited thereto.

As such, the organic compound according to the present invention can synthesize organic compounds having various characteristics using a characteristic skeleton exhibiting intrinsic characteristics and a moiety having intrinsic characteristics introduced thereto, and as a result The organic compound according to the present invention can be applied to various organic layer materials such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. In addition, even when employed in the light efficiency improving layer provided in the organic light emitting device, it is possible to improve light emitting characteristics such as light emitting efficiency.

In addition, the compound of the present invention can be applied to a device according to a general method for manufacturing an organic light emitting device.

The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween, except that the organic compound according to the present invention is used in the organic layer of the device. and can be manufactured using conventional device manufacturing methods and materials.

The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, but may have a multi-layered structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a light efficiency improving layer (Capping layer) and the like. However, the present invention is not limited thereto and may include a smaller number or a larger number of organic layers.

In addition, the organic electroluminescent device according to an embodiment of the present invention includes a substrate, a first electrode (anode), an organic layer, a second electrode (cathode) and a light efficiency improving layer, wherein the light efficiency improving layer is a lower portion of the first electrode ( Bottom emission) or on the second electrode top (Top emission).

In the method of forming the second electrode upper (Top emission), the light formed in the light emitting layer is emitted toward the cathode, and the light emitted toward the cathode passes through the light efficiency improvement layer (CPL) formed of the compound according to the present invention having a relatively high refractive index. The wavelength is amplified and thus the luminous efficiency is increased. In addition, the light efficiency of the organic electric device is improved by employing the compound according to the present invention in the light efficiency improving layer according to the same principle as the method formed in the lower portion of the first electrode (Bottom emission).

The organic layer structure of the preferred organic light emitting device according to the present invention will be described in more detail in the following Examples.

In addition, the organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method, such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition to this method, an organic light emitting diode may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed in a smaller number by a solvent process rather than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , a conductive polymer such as polypyrrole and polyaniline, but is not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, and multilayered materials such as LiF/Al or LiO ₂ /Al Structural materials and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, and polythiophene-based conductive polymers, and the like, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. can be further improved.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and Benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but are not limited thereto.

As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex including Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex.

The organic light emitting diode according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.

In addition, the organic compound according to the present invention may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, an organic transistor, and the like.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, the scope of the present invention is not limited thereby, and it is common in the art that various changes and modifications are possible within the scope and spirit of the present invention. It will be obvious to those with knowledge.

Synthesis example 1: Synthesis of compound 1

(One) production example 1: Synthesis of Intermediate 1-1

3,6-Dibromocarbazole (10.0 g, 0.031 mol), 4-Fluorobenzonitrile (4.47 g, 0.037 mol), Cs ₂ CO ₃ (6.38 g, 0.046 mol), 150 mL of DMF was added and stirred under reflux at 150 ° C for 12 hours. and reacted. After completion of the reaction, 10.0 g (yield 76.3%) of <Intermediate 1-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 1-2

Intermediate 1-1 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (9.14 g, 0.046 mol), KOAc (15.94 g, 0.115 mol), Pd(dppf)Cl ₂ (10.44 g, 0.4 mmol) in Dioxane 120 mL was added, and the reaction was stirred under reflux at 100 °C for 12 hours. After completion of the reaction, 9.1 g (yield 74.5%) of <Intermediate 1-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 1

Toluene in Intermediate 1-2 (10.0 g, 0.019 mol), 2-Bromobenzoxazole (9.14 g, 0.046 mol), K ₂ CO ₃ (15.94 g, 0.115 mol), Pd(PPh ₃ ) ₄ (0.44 g, 0.4 mmol) 100 mL, 25 mL of EtOH, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 6.7 g (yield 69.4%) of <Compound 1> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=502[(M+1) ⁺ ]

Synthesis example 2: Synthesis of compound 16

(One) production example 1: Synthesis of Intermediate 16-1

Add 150 mL of DMF to 3,6-Dibromocarbazole (10.0 g, 0.031 mol), 2-Fluorobenzonitrile (4.47 g, 0.037 mol), Cs ₂ CO ₃ (6.38 g, 0.046 mol) and stir under reflux at 150 ° C for 12 hours. reacted. After completion of the reaction, 9.9 g (yield 75.5%) of <Intermediate 16-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 16-2

Dioxane 120 in Intermediate 16-1 (10.0 g, 0.024 mol), Bis(pinacolato)diboron (14.30 g, 0.056 mol), KOAc (9.21 g, 0.094 mol), Pd(dppf)Cl ₂ (1.03 g, 0.001 mol) mL was added, and the reaction was stirred under reflux at 100 °C for 12 hours. After completion of the reaction, 8.34 g (yield 68.3%) of <Intermediate 16-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 16

Intermediate 16-2 (10.0 g, 0.019 mol), 2-Bromobenzoxazole (9.14 g, 0.046 mol), K ₂ CO ₃ (15.94 g, 0.115 mol), Pd(PPh ₃ ) ₄ (0.44 g, 0.4 mmol) in Toluene 100 mL, 25 mL of EtOH, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 6.8 g (yield 70.4%) of <Compound 16> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=502[(M+1) ⁺ ]

Synthesis example 3: Synthesis of compound 26

(One) production example 1: Synthesis of Intermediate 26-1

9-(4-Bromophenyl)-carbazole (10.0 g, 0.031 mol), 4-Cyanophenylboronic acid (5.47 g, 0.037 mol), K ₂ CO ₃ (12.87 g, 0.093 mol), Pd(PPh ₃ ) ₄ (0.72 g , 0.6 mmol), 150 mL of Toluene, 38 mL of EtOH, and 38 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 8.3 g (yield 77.7%) of <Intermediate 26-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of Intermediate 26-2

150 mL of DMF was added to Intermediate 26-1 (10.0 g, 0.029 mol) and N-Bromosuccinimide (12.4 g, 0.070 mol), and the reaction was stirred under reflux at room temperature for 5 hours. After completion of the reaction, after extraction and concentration, <Intermediate 26-2> was obtained by column 9.86 g (yield 67.6%).

(3) production example 3: Synthesis of Intermediate 26-3

Intermediate 26-2 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (12.14 g, 0.048 mol), KOAc (7.82 g, 0.08 mol), Dioxane 100 in Pd(dppf)Cl ₂ (0.87 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.5 g (yield 71.6%) of <Intermediate 26-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) production example 4: Synthesis of compound 26

Intermediate 26-3 (10.0 g, 0.017 mol), 2-Bromobenzoxazole (7.97 g, 0.040 mol), K ₂ CO ₃ (13.91 g, 0.101 mol), Pd(PPh ₃ ) ₄ (0.39 g, 0.3 mmol) in Toluene 100 mL, 25 mL of Ethanol, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 6.8 g (yield 70.1%) of <Compound 26> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=578 [(M+1) ⁺ ]

Synthesis example 4: Synthesis of compound 30

(One) production example 1: Synthesis of Intermediate 30-1

2-Bromobenzonitrile (10.0 g, 0.055 mol), 4-(9-Carbazolyl)phenylboronic acid (15.44 g, 0.066 mol), K ₂ CO ₃ (22.78 g, 0.165 mol), Pd(PPh ₃ ) ₄ (1.27 g, 0.001 mol) was added to 280 mL of Toluene, 70 mL of EtOH, and 70 mL of H ₂ O, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 15.7 g (yield 83.0%) of <Intermediate 30-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 30-2

150 mL of DMF was added to Intermediate 30-1 (10.0 g, 0.029 mol) and N-Bromosuccinimide (12.4 g, 0.070 mol), and the reaction was stirred under reflux at room temperature for 5 hours. After completion of the reaction, 10.0 g (yield 68.6%) of <Intermediate 30-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 30-3

Intermediate 30-2 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (12.14 g, 0.048 mol), KOAc (7.82 g, 0.080 mol), Dioxane 100 in Pd(dppf)Cl ₂ (0.87 g, 0.001 mol) mL was added, and the reaction was stirred under reflux at 100 °C for 12 hours. After completion of the reaction, 14.5 g (yield 75.4%) of <Intermediate 30-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) production example 4: Synthesis of compound 30

Toluene in Intermediate 30-3 (10.0 g, 0.017 mol), 2-Bromobenzoxazole (7.97 g, 0.040 mol), K ₂ CO ₃ (13.91 g, 0.101 mol), Pd(PPh ₃ ) ₄ (0.39 g, 0.3 mmol) 100 mL, 25 mL of EtOH, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 5.94 g (yield 70.5%) of <Compound 30> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=578 [(M+1) ⁺ ]

Synthesis example 5: Synthesis of compound 31

(One) production example 1: Synthesis of intermediate 31-1

4-Bromobenzonitrile (10.0 g, 0.055 mol), 3-(9-Carbazolyl)phenylboronic acid (17.35 g, 0.066 mol), K ₂ CO ₃ (22.78 g, 0.165 mol), Pd(PPh ₃ ) ₄ (1.27 g, 0.001 mol), 275 mL of Toluene, 69 mL of EtOH, and 69 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 15.0 g (yield 79.3%) of <Intermediate 31-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 31-2

150 mL of DMF was added to Intermediate 31-1 (10.0 g, 0.029 mol) and N-Bromosuccinimide (18.6 g, 0.070 mol), and the reaction was stirred under reflux at room temperature for 5 hours. After completion of the reaction, 9.7 g (yield 66.5%) of <Intermediate 31-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 31-3

Intermediate 31-2 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (12.14 g, 0.048 mol), KOAc (7.82 g, 0.080 mol), Dioxane 100 in Pd(dppf)Cl ₂ (0.87 g, 0.001 mol) mL was added, and the reaction was stirred under reflux at 100 °C for 12 hours. After completion of the reaction, 8.4 g (yield 70.7%) of <Intermediate 31-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) production example 4: Synthesis of intermediate 31

Intermediate 31-3 (10.0 g, 0.017 mol), 2-Bromobenzoxazole (7.97 g, 0.040 mol), K ₂ CO ₃ (13.91 g, 0.101 mol), Pd(PPh ₃ ) ₄ (0.39 g, 0.3 mmol) in Toluene 100 mL, 25 mL of EtOH, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 6.8 g (yield 70.0%) of <Compound 31> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=578 [(M+1) ⁺ ]

Synthesis example 6: Synthesis of compound 35

(One) production example 1: Synthesis of intermediate 35-1

Dioxane in 3,6-Dibromocarbazole (10.0 g, 0.031 mol), Bis(pinacolato)diboron (18.75 g, 0.074 mol), KOAc (12.08 g, 0.123 mol), Pd(dppf)Cl ₂ (1.35 g, 0.002 mol) 155 mL was added, and the reaction was stirred at 100 °C for 12 hours. After completion of the reaction, 9.9 g (yield 80.2%) of <Intermediate 35-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 35-2

Intermediate 35-1 (10.0 g, 0.024 mol), 2-Bromobenzoxazole (11.34 g, 0.057 mol), K ₂ CO ₃ (19.79 g, 0.143 mol), Pd(PPh ₃ ) ₄ (0.55 g, 0.5 mmol) in Toluene 120 mL, 30 mL of EtOH, 30 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 7.2 g (yield 75.2%) of <Intermediate 35-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 35-3

Intermediate 35-2 (10.0 g, 0.025 mol), 1-Bromo-2-fluorobenzene (7.59 g, 0.030 mol), Cs ₂ CO ₃ (5.16 g, 0.037 mol) Add 130 mL of DMF to 150 ℃ for 12 hours. The reaction was stirred under reflux. After completion of the reaction, 9.8 g (yield 70.7%) of <Intermediate 35-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) production example 4: Synthesis of compound 35

Intermediate 35-3 (10.0 g, 0.018 mol), 4-Cyanophenylboronic acid (3.17 g, 0.022 mol), K ₂ CO ₃ (7.45 g, 0.054 mol), Pd(PPh ₃ ) ₄ (0.42 g, 0.4 mmol) Toluene 120 mL, EtOH 30 mL, H ₂ O 30 mL were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 6.8 g (yield 65.4%) of <Compound 35> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=578 [(M+1) ⁺ ]

Synthesis example 7: Synthesis of compound 38

(One) production example 1: Synthesis of intermediate 38-1

To 5-Hydroxyisophthalonitrile (10.0 g, 0.069 mol), Et ₃ N in dichloromethane (9.78 g, 0.153 mol), Tf ₂ O (19.7 g, 0.153 mol) is added dropwise dropwise. After slowly raising to room temperature, the reaction was stirred under reflux for 12 hours. After completion of the reaction, 16.7 g (yield 87.2%) of <Intermediate 38-1> was obtained by extraction and column purification.

(2) production example 2: Synthesis of intermediate 38-2

Intermediate 38-1 (10.0 g, 0.036 mol), 4-(9-Carbazolyl)phenylboronic acid (12.47 g, 0.043 mol), K ₂ CO ₃ (15.01 g, 0.109 mol), Pd(PPh ₃ ) ₄ (0.84 g , 0.7 mmol), 180 mL of Dioxane and 18 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 4 hours. After completion of the reaction, 9.9 g (yield 74.0%) of <Intermediate 38-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 38-3

Intermediate 38-2 (10.0 g, 0.027 mol), N-Bromosuccinimide (11.6 g, 0.065 mol) was added with 140 mL of DMF, followed by stirring under reflux at room temperature for 5 hours. After completion of the reaction, 9.1 g (yield 63.8%) of <Intermediate 38-3> was obtained by extraction, concentration, and column.

(4) production example 4: Synthesis of intermediate 38-4

Intermediate 38-3 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (11.56 g, 0.046 mol), KOAc (7.45 g, 0.076 mol), Dioxane 100 in Pd(dppf)Cl ₂ (0.83 g, 0.001 mol) mL was added, and the reaction was stirred under reflux at 100 °C for 12 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.9 g (yield 67.0%) of <Intermediate 38-4>.

(5) production example 5: Synthesis of compound 38

Intermediate 38-4 (10.0 g, 0.016 mol), 2-Bromobenzoxazole (7.65 g, 0.039 mol), K ₂ CO ₃ (13.35 g, 0.097 mol), Pd(PPh ₃ ) ₄ (0.37 g, 0.3 mmol) in Toluene 100 mL, 25 mL of EtOH, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 6.2 g (yield 63.8%) of <Compound 38> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=603[(M+1) ⁺ ]

Synthesis example 8: Synthesis of compound 43

(One) production example 1: Synthesis of intermediate 43-1

4-Bromo-1-naphthonitrile (10.0 g, 0.043 mol), 4-(9H-carbazol-9-yl)phenylboronic acid (14.85 g, 0.052 mol), K ₂ CO ₃ (17.87 g, 0.129 mol), Pd ( Toluene 220 mL, EtOH 55 mL, and H ₂ O 55 mL were added to PPh ₃ ) ₄ (1.00 g, 0.9 mmol), and the reaction was stirred under reflux at 100° C. for 6 hours. After completion of the reaction, 13.5 g (yield 79.4%) of <Intermediate 43-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of intermediate 43-2

130 mL of DMF was added to Intermediate 43-1 (10.0 g, 0.025 mol) and N-Bromosuccinimide (10.8 g, 0.061 mol), and the reaction was stirred under reflux at room temperature for 5 hours. After completion of the reaction, 9.2 g (yield 65.7%) of <Intermediate 43-2> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 43-3

Intermediate 43-2 (10.0 g, 0.021 mol), Bis(pinacolato)diboron (12.80 g, 0.050 mol), KOAc (8.24 g, 0.084 mol), Dioxane 100 in Pd(dppf)Cl ₂ (0.92 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 17.4 g (yield 76.2%) of <Intermediate 43-3> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 43

Intermediate 43-3 (10.0 g, 0.018 mol), 2-Bromobenzoxazole (8.33 g, 0.042 mol), K ₂ CO ₃ (14.54 g, 0.105 mol), Pd(PPh ₃ ) ₄ (0.41 g, 0.4 mmol) in Toluene 100 mL, 25 mL of EtOH, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 7.1 g (yield 73.3%) of <Compound 43> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=628[(M+1) ⁺ ]

Synthesis example 9: Synthesis of compound 45

(One) production example 1: Synthesis of intermediate 45-1

3,6-Dibromocarbazole (10.0 g, 0.031 mol), 4-Fluoro-1-naphthonitrile (6.32 g, 0.037 mol), Cs ₂ CO ₃ (6.38 g, 0.046 mol) Add 155 mL of DMF to 150 °C for 12 hours. The reaction was stirred at reflux. After completion of the reaction, 11.2 g (yield 76.4%) of <Intermediate 45-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 45-2

Intermediate 45-1 (10.0 g, 0.021 mol), Bis(pinacolato)diboron (12.80 g, 0.050 mol), KOAc (8.24 g, 0.084 mol), Pd(dppf)Cl ₂ (0.92 g, 0.001 mol) in Dioxane 100 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.6 g (yield 71.8%) of <Intermediate 45-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 45

Intermediate 45-2 (10.0 g, 0.018 mol), 2-Bromobenzoxazole (8.33 g, 0.042 mol), K ₂ CO ₃ (14.54 g, 0.105 mol), Pd(PPh ₃ ) ₄ (0.41 g, 0.4 mmol) in Toluene 100 mL, 25 mL of EtOH, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 5.9 g (yield 61.0%) of <Compound 45> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=552[(M+1) ⁺ ]

Synthesis example 10: Synthesis of compound 55

(One) production example 1: Synthesis of intermediate 55-1

Add 130 mL of DMF to Intermediate 35-2 (10.0 g, 0.025 mol), 1,3-Dibromo-5-fluorobenzene (7.59 g, 0.030 mol), Cs ₂ CO ₃ (5.16 g, 0.037 mol) and 150 for 12 hours The reaction was stirred under reflux at ℃. After completion of the reaction, 12.1 g (yield 75.8%) of <Intermediate 55-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of compound 55

Intermediate 55-1 (10.0 g, 0.016 mol), 4-Cyanophenylboronic acid (5.55 g, 0.038 mol), K ₂ CO ₃ (13.05 g, 0.094 mol), Pd(PPh ₃ ) ₄ (0.36 g, 0.3 mmol) Toluene 80 mL, EtOH 20 mL, H ₂ O 20 mL were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 6.8 g (yield 63.6%) of <Compound 55> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=679[(M+1) ⁺ ]

Synthesis example 11: Synthesis of compound 65

(One) production example 1: Synthesis of compound 65

Intermediate 1-2 (10.0 g, 0.019 mol), 2-Bromobenzothiazole (9.88 g, 0.046 mol), K ₂ CO ₃ (15.94 g, 0.115 mol), Pd(PPh ₃ ) ₄ (0.44 g, 0.4 mmol) in Toluene 100 mL, 25 mL of EtOH, 25 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.2 g (yield 70.0%) of <Compound 65>.

LC/MS: m/z=534 [(M+1) ⁺ ]

device Example (capping layer)

In the embodiment according to the present invention, the anode was cleaned using an ITO glass substrate containing 25 mm × 25 mm × 0.7 mm Ag, after patterning so that the light emitting area has a size of 2 mm × 2 mm. After the patterned ITO substrate was mounted in a vacuum chamber, organic materials and metals were deposited on the substrate in the following structure at a process pressure of 1 × 10 ^-6 torr or more.

device Example 1 to 20

By employing the compound implemented according to the present invention in the light efficiency improving layer, a blue organic light emitting device having the following device structure was manufactured, and then light emission and driving characteristics according to the compound implemented according to the present invention were measured.

Ag/ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (TCTA, 10 nm) / light emitting layer (20 nm) / electron transport layer (201: Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / Light efficiency improvement layer (70 nm)

[HAT-CN] was formed on a glass substrate to a thickness of 5 nm on an ITO transparent electrode containing Ag to form a hole injection layer, and then [α-NPB] was formed to a thickness of 100 nm to form a hole transport layer, [TCTA] was deposited to a thickness of 10 nm to form an electron blocking layer, and a light emitting layer was formed by co-deposition at 20 nm using [BH1] as a host compound and [BD1] as a dopant compound, and an electron transport layer ( ] After depositing the compound Liq 50% doping) at 30 nm, LiF was formed to a thickness of 1 nm to form an electron injection layer, and Mg:Ag was formed to a thickness of 15 nm in a ratio of 1:9 to form a cathode. , the light efficiency improving layer (capping layer) was prepared by forming an organic light emitting device by forming a film of the compound implemented in the present invention described in [Table 1] to a thickness of 70 nm.

device comparative example One

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner except that the light efficiency improving layer was not used in the device structure of Example 1.

device comparative example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner except that Alq ₃ was used instead of the compound of the present invention as the light efficiency improving layer compound in the device structure of Example 1.

device comparative example 3

The organic light emitting device for Device Comparative Example 3 was manufactured in the same manner except that CP1 was used instead of the compound of the present invention as the light efficiency improving layer compound in the device structure of Example 1.

device comparative example 4

An organic light emitting device for Device Comparative Example 4 was manufactured in the same manner except that CP2 was used instead of the compound of the present invention as the light efficiency improving layer compound in the device structure of Example 1.

Experimental example 1: element Example 1 to 20 luminescent properties

The driving voltage, current efficiency and color coordinates were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) for the organic light emitting diodes manufactured according to the Examples and Comparative Examples, 1,000 nit standard The result value of is shown in [Table 1] below.

Example	Light Efficiency Improvement Layer	V	cd/A	CIEx	CIEy
One	Formula 1	3.7	8.5	0.139	0.051
2	Formula 16	3.8	8.1	0.140	0.050
3	Formula 21	3.6	8.8	0.143	0.048
4	Formula 26	3.5	8.9	0.139	0.054
5	Formula 30	3.7	8.5	0.138	0.053
6	Formula 31	3.5	8.9	0.142	0.051
7	Formula 35	3.7	8.3	0.143	0.048
8	Formula 43	3.6	8.7	0.141	0.053
9	Formula 45	3.7	8.4	0.139	0.056
10	Formula 55	3.6	8.8	0.141	0.051
11	Formula 65	3.8	8.2	0.141	0.050
12	Formula 80	3.7	8.6	0.143	0.048
13	Formula 89	3.4	9.0	0.141	0.052
14	Formula 91	3.7	8.5	0.138	0.053
15	Formula 93	3.8	8.1	0.141	0.050
16	Formula 94	3.6	8.8	0.140	0.049
17	Formula 97	3.5	8.9	0.139	0.055
18	Formula 103	3.7	8.5	0.140	0.048
19	Formula 108	3.5	8.9	0.140	0.049
20	Formula 119	3.7	8.3	0.141	0.049
Comparative Example 1	not used	4.2	7.0	0.146	0.141
Comparative Example 2	Alq 3	4.0	7.5	0.144	0.062
Comparative Example 3	CP1	3.9	8.0	0.138	0.058
Comparative Example 4	CP2	3.9	7.8	0.135	0.061

Looking at the results shown in [Table 1], when the compound according to the present invention is applied to a device as a light efficiency improving layer, a device that does not employ a conventional light efficiency improving layer, a compound used as a conventional light efficiency improving layer material, and a compound according to the present invention It can be seen that the driving voltage is decreased and the current efficiency is improved compared to the devices (Comparative Examples 1 to 4) each employing the compound having the structural characteristics contrasting with the structural characteristics.

[HAT-CN] [α-NPB] [BH1] [BD1] [201]

[TCTA] [CP1] [CP2]

device Example ( ETL )

In an embodiment according to the present invention, the ITO transparent electrode is patterned so that the light emitting area is 2 mm × 2 mm in size, using an ITO glass substrate to which an ITO transparent electrode is attached, on a glass substrate of 25 mm × 25 mm × 0.7 mm After that, it was washed. After the substrate was mounted in a vacuum chamber and the base pressure was set to 1 × 10 ^-6 torr or more, the organic material and the metal were deposited on the ITO in the following structure.

device Example 21 to 31

The compound implemented according to the present invention was used as the electron transport layer. A blue organic light emitting device having the following device structure was manufactured, and light emitting characteristics including current efficiency were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (EBL1 10 nm) / light emitting layer (20 nm) / hole blocking layer (HBL1, 50 nm) / Electron transport layer (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

To form a hole injection layer on the ITO transparent electrode, it was deposited at 5 nm using [HAT-CN], the hole transport layer was formed at 100 nm using α-NPB, and the electron blocking layer was 10 using [EBL1]. It was deposited to a thickness of nm, and [BH1] was used as a host compound for the emission layer, and [BD1] was used as a dopant compound to be co-deposited to a thickness of 20 nm. In addition, the electron transport layer was formed into a film to a thickness of 30 nm (Liq doping) using the compound embodied in the present invention described in [Table 2] below. An organic light emitting diode was manufactured by forming a film of 1 nm LiF and 100 nm of Al.

device comparative example 5

The organic light emitting device for Device Comparative Example 5 was manufactured in the same manner except that the following [201] was used instead of the compound embodied in the present invention in the electron transport layer in the device structure of Example 21.

device comparative example 6

The organic light emitting device for Device Comparative Example 6 was manufactured in the same manner except that the following [ET1] was used instead of the compound embodied in the present invention in the electron transport layer in the device structure of Example 21.

device comparative example 7

The organic light emitting device for Device Comparative Example 7 was manufactured in the same manner except that the following [ET2] was used instead of the compound embodied in the present invention for the electron transport layer in the device structure of Example 21.

Experimental example 2: element Example 21 to 31 luminescence characteristics

For the organic light emitting devices manufactured according to the above Examples and Comparative Examples, voltage, current and luminous efficiency were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), 1000 nit standard The result value of is shown in [Table 2] below.

Example	electron transport layer	V	cd/A	CIEx	CIEy
21	Formula 1	4.3	6.9	0.133	0.148
22	Formula 16	4.5	7.2	0.132	0.149
23	Formula 26	4.5	7.1	0.130	0.151
24	Formula 30	4.5	7.1	0.131	0.151
25	Formula 38	4.4	7.2	0.134	0.149
26	Formula 65	4.5	7.2	0.132	0.148
27	Formula 80	4.6	7.1	0.133	0.149
28	Formula 89	4.4	7.3	0.134	0.152
29	Formula 93	4.4	7.2	0.131	0.152
30	Formula 94	4.2	7.0	0.132	0.150
31	Formula 97	4.5	7.0	0.131	0.148
Comparative Example 5	201	4.7	6.6	0.135	0.151
Comparative Example 6	ET1	5.7	4.9	0.135	0.130
Comparative Example 7	ET2	5.8	4.8	0.133	0.133

Looking at the results shown in [Table 2], when the compound according to the present invention is applied to the electron transport layer in the device, the characteristic structure of the compound [201] used as the conventional electron transport layer material and the compound according to the present invention has a difference It can be seen that the light emitting characteristics such as low voltage driving and luminous efficiency are significantly superior to the devices employing [ET1] and [ET2] (Comparative Examples 5 to 7).

[HAT-CN] [α-NPB] [BH1] [BD1] [201]

[EBL1] [ET1] [ET2]

When the organic compound according to the present invention is employed as a material for an organic layer in an organic light emitting device or a light efficiency improvement layer provided in an organic light emitting device, it is possible to realize light emitting characteristics such as low voltage driving and excellent luminous efficiency of the device, so that it can be used in various lighting and display devices. It can be usefully used industrially.

Claims (9)

1. An organic compound represented by the following [Formula I]:

   [Formula Ⅰ]

   

   In the [Formula I],

   Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in which at least one cyano group (CN) is substituted (m is an integer of 1 or 2, and when m is 2, a plurality of Ars are the same or different from each other) ),

   L is a single bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms (n is an integer of 0 to 2, and when n is 2, a plurality of L's are the same or different from each other),

   R ₁ to R ₂ are each independently represented by the following [Structural Formula 1],

   [Structural Formula 1]

   

   In the [Structural Formula 1],

   X is O or S, Z is CR (a plurality of R are the same or different from each other),

   R and R ₃ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C 3 to 20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 halogenated alkyl group, substituted or unsubstituted C1-C20 halogenated alkoxy group, substituted or It is selected from an unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group,

   Any one of the plurality of R and R ₃ is a moiety connected in [Formula I] at the positions of R ₁ and R ₂ in which [Structural Formula 1] is, respectively,

   The plurality of R and R ₃ may be bonded to each other or connected to an adjacent substituent to form an aromatic monocyclic or polycyclic ring.
2. The method of claim 1,

   The [Structural Formula 1] is an organic compound, characterized in that any one selected from the structural formulas represented by the following [Structural Formula 2] to [Structural Formula 6]:

   [Structural formula 2] [Structural formula 3] [Structural formula 4]

   

   [Structural formula 5] [Structural formula 6]

   

   In the [Structural Formula 2] to [Structural Formula 6],

   X is O or S, Z is CR (a plurality of R are the same or different from each other),

   R and R ₃ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C 3 to 20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 halogenated alkyl group, substituted or unsubstituted C1-C20 halogenated alkoxy group, substituted or It is selected from an unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,

   Any one of the plurality of R and R ₃ is a moiety in which [Formula 1] is connected in [Formula I] at the positions of R ₁ and R ₂ , respectively.
3. 3. The method of claim 1 or 2,

   In the above definitions of Ar, L, R and R ₃ , 'substituted or unsubstituted' means deuterium, a halogen group, a cyano group, a nitro group, a hydroxy group, a silyl group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, substituted with one or more substituents selected from the group consisting of a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, an alkylamine group, an arylamine group, and a silyl group; , An organic compound characterized in that it is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
4. The method of claim 1,

   The [Formula I] is an organic compound, characterized in that any one selected from the following [Compound 1] to [Compound 134]:

   

   

   

   

   

   

   

   

   

   

   

   

   
5. An organic light emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode,

   At least one of the organic layers is an organic light emitting device comprising the organic compound of [Formula I] according to claim 1.
6. 6. The method of claim 5,

   The organic layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer, and a light emitting layer including one or more floors that become

   At least one of the layers comprises an organic compound represented by the [Formula I].
7. 6. The method of claim 5,

   An organic light emitting device comprising an organic compound represented by the above [Formula I] in any one of the electron transport layer, the electron injection layer, and the layer performing both electron transport and electron injection functions.
8. 6. The method of claim 5,

   Further comprising a light efficiency improvement layer (Capping layer) formed on at least one side opposite to the organic layer among the upper or lower portions of the first electrode and the second electrode,

   The light efficiency improving layer is an organic light emitting device, characterized in that it comprises an organic compound represented by the [Formula I].
9. 9. The method of claim 8,

   The light efficiency improving layer is an organic light emitting device, characterized in that formed on at least one of a lower portion of the first electrode or an upper portion of the second electrode.